Citation: Rui Jian, Zhang Qi, Wang Xin, Xu Xu, Xu Haijun, Rao Weidong, Wang Shifa. Synthesis and Biological Activity of Novel Pinanyl Pyrazole Acetamide Derivatives[J]. Chinese Journal of Organic Chemistry, ;2017, 37(1): 218-225. doi: 10.6023/cjoc201606038 shu

Synthesis and Biological Activity of Novel Pinanyl Pyrazole Acetamide Derivatives

Rui Jian ^a ,
Zhang Qi ^a ,
Wang Xin ^b ,
Xu Xu ^a,c,d ,
Xu Haijun ^a ,
Rao Weidong ^a ,
Wang Shifa ^a,c,d,*,,

a.
College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037
b.
College of Plant Protection, Nanjing Agricultural University, Nanjing 210095
c.
Jiangsu Key Laboratory of Biomass-based Green Fuels and Chemicals, Nanjing 210037
d.
Guangxi Key Laboratory of Chemistry and Engineering of Forest Products, Nanning 530008

Corresponding author: Wang Shifa, wsfyyq@njfu.com.cn
Received Date: 24 June 2016
Revised Date: 4 August 2016

Fund Project: the Natural Science Foundation of the Jiangsu Higher Education Institutions of China 14KJ220001the National Natural Science Foundation of China 31470529the Open Funding of Guangxi Key Laboratory of Chemistry and Engineering of Forest Products GXFC15-02

Figures(2)

Novel pinanyl pyrazole derivatives were synthesized from nopinone and their bioactivities were also examined in this paper.The intermediate compounds 3-arylidenenopinones 2a~2g were synthesized by condensation of aromatic aldehydes and nopinone, and pinanyl pyrazole derivatives 3a~3g were subsequently obtained by cyclization and dehydroaromatization of compounds 2a~2g and hydrazine hydrate in the circumstance of N, N-dimethylformamide (DMT).The target compound pinanyl pyrazole acetamide derivatives 4a~4g were synthesized by alkylation using 2-chloroacetamide as the alkylating agent under the condition of base catalysis.The structures of synthesized compounds were characterized by ¹H NMR, ¹³C NMR, IR, HRMS, and X-ray diffraction analysis.Biological activities evaluation of compounds 3a~3g and 4a~4g were performed including antibacterial and insecticidal activities on Tinocallis kahawaluokalani.Test results showed that compound 4g was a more potent bactericide and fungicide than others because of its good activities against bacteria and fungi; furthermore, compound 4g had shown the better insecticidal activity against Tinocallis kahawaluokalani than the others.
- nopinone,
- pinanyl pyrazole derivatives,
- bacteriostatic activity,
- insecticidal activity
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